The Homecoming Bet
by Vstriker
Summary: With a school dance approaching Ash and friends decide to make a bet to see who can actually get a date. But things may get more complicated then expected when they decide to choose each others 'Targets'. How out of hand can things possibly get though?


Ash stared down at the paper grimly and grinded his teeth. Out of all the things he had to deal with in high school he never thought that this would be the most challenging. The biggest obstacle he had to face yet. "Ash! Why do you keep staring at that flyer for like that? It's a school dance, not an all you can eat buffet." Gary said looking over the boys shoulder. Ash didn't even look away and frankly Gary was starting to worry. "Earth to Ashy boy! You home?"

"He's probably just worried that this is the first school dance everyone is expected to bring a date to. We're not freshman anymore dude, we come alone and we're marked losers for the rest of high school. And you know what that could lead to." Kenny said stringing his guitar.

"Low self esteem? A lifetime of loneliness? Baldness?" Barry guessed taking a bite of an apple. They all looked towards him and he shrugged. "What? We all know it's true."

"I don't think bringing a date is that big a deal guys. I mean it's not like we're upperclassmen. Who's even paying attention to us? We're under the radar. I don't even think people would notice if we didn't come." Ritchie said as he took a seat next to Ash.

Drew chuckled and flipped his hair back. "All the upperclassmen will be watching us. The juniors this year will be seniors next year, and like it or not they'll have a lot of say on where we stand on the food chain. Saying it isn't important or not showing up could be the death sentence of high school." He said pulling out a comb and running it through his hair.

Paul gave a grunt. "You're all suckers for even caving in to this high school popularity crap. It's a waste of time. I'm here to wreck some things at a few house parties, drink some beer, get my diploma, and get the hell out of here." He said as he smashed his fist into the punching bag he hung up on the oak tree near their table.

A flash distracted everyone and they all turned towards Trip who was holding his camera up and snapping another photo. They glared at him and he simply returned it. "I'm a photographer, and you all became friends with me knowing that. Don't complain now." He said turning and snapping another picture. "Besides, I don't see what's so hard about asking a girl out."

Ash crumpled the paper up and shot around to look at Trip. "Are you kidding me? Girls are the hardest thing to deal with on the planet! Their nice and then suddenly mean as scorpions, they cry out of nowhere and make you feel guilty, and they're the most confusing creatures on the planet! They're impossible to read and their just… crazy!" Ash ranted while running his hands through his hair. "How am I supposed to ask a girl to a dance? They're all so backwards."

Conversations usually went just like this during their lunch. Ever since freshman year they ate outside, talked about what was bothering them, did last minute homework, and whatever else they felt like. The table used to belong to the seniors last year, but lucky for them Barry was able to speed his way here and stake a claim this year. Track team had paid off. "Are you kidding me? Why don't you just ask Misty."

"What? Misty would be more like a friend, and we need to get serious dates here. The friend stuff won't cut it anymore." Ash argued. They looked at him as if he was the dumbest man on the planet, and half of them were pretty sure he was. "What?"

"She likes you dude." Ritchie stated as if it was the most obvious thing in the world.

"What?" Ask yelled.

"How could you not know that? She's been following you around since you guys were in the fifth grade!" Gary said shaking his head at his friend. Ash and he were like brothers, but he could be more dense then a diamond.

Ash looked at him confusingly. "But I thought it was because I wrecked her bike?" He asked.

"For like the first year! But then it was just an excuse man!"

Ash looked up in the air in deep thought as the others either gave a sigh or laughed. Except Paul who just kept throwing blows at his punching bag. "Forget it man. Even if you had realized it earlier you never would have had the guts to ask her out. You don't have a single clue about girls." Trip said as the others laughed.

Ash glared at them. "Like I'm the only one! I don't see any of you guys with a girl around you're arm!" He said pointing at them all.

Drew scoffed. "Please. Me Paul and Gary have girls swarming all over us. It's you Barry and Ritchie that are always struggled. And Trip is only okay with the ladies." He said smirking.

"Funny how you can get every girl except the one you actually want to get with. Girls swoon all over you, but the minute May walks in it's like all that smooth swagger goes straight in the trash." Trip countered.

"And Gary hasn't kept the same girl for more than a month! It'll be a wonder if he doesn't have a reputation by now!" Barry said pointing at the brown haired boy.

Paul snickered. "At least he can keep a girl." He muttered.

"Maybe I'll ask Zoey." Barry asked smiling. Paul, though only for a second, hesitated. He then swung full force and slammed his fist into the bag. He turned around and glared at Barry who was snickering.

"Like I care…" He went back to punching as if he had never entered the conversation in the first place.

Everyone went back to glaring at each other and eventually a smirk came across Gary's face. "I say we settle this just like we always do." They knew what he was referring too. Whenever there were rumors of a fight, they would throw in money and place bets. It was something they had started in middle school when it was just Ash, Gary, and Ritchie. "Whoever can actually get a date wins. How about it?"

"How much we putting in?" Drew asked confidently.

"Time out! There are a few things wrong here! We need to rework this!" Ash said standing up.

"What's the matter, not up to it?" Gary asked.

Everyone looked towards Ritchie who was raising his hand. "It's not like I'm not interest, but I do think Ash had a point. Gary, Paul, and Drew would be able to walk outside and complete this bet no problem. It would be a surefire win for them. It should be more challenging shouldn't it? Instead of just picking out any girl it should be specific. That way it'll be more fair towards everyone, wouldn't it?"

Everyone thought over it for a second. Ritchie did have a point, and it did seem more interesting that way. "I'm in." Drew said smirking. He threw in a twenty.

"Let's do this." Gary said throwing his piece in. "You game Ash?"

"Me? I'm big game." He said smiling. He tossed his bill in as well." Paul?"

"Whatever…" Was all they heard before he tossed his twenty in.

Barry cracked his knuckles and then tossed his share in. "This is my type of challenge. Cause no matter what girl you pick no one can resist the old Barry swag."

"Except every living girl on the planet. I'm in to." Trip said taking out his twenty and throwing it in. "And what about you Ritchie?"

"I guess so." He said rubbing the back of his head.

"Well I'm in." Kenny said smiling. "Whatever. So, how are we going to decide who our targets are going to be?"

"We'll all just vote for each other. Whose first." Gary proposed.

"Me!" Ash yelled.

"Misty." Everyone answered in unison and Ash looked around bewildered.

"What? That's not fair!"

Kenny laughed. "You wanted to go first. Though you were probably going to get Misty anyway man. You two have been like glue so it's pretty obvious." He said playing off a few notes from his guitar. "I guess I'll go next."

Gary rubbed his chin and thought for a moment. "How about Dawn?"

The string on Kenny's guitar snapped and he grew wide eyed. "What? No! She's like my best friend, plus we're in the same band! It'll just make things complicated." He said blushing.

"In that case it's definitely Dawn." Drew said clapping his hands together. "What challenge will you guys bring for me? One of the Cerulean sisters? Whitney? Or maybe Flannery? I'd love to take a crack at Elesa."

"Or maybe May?" Ash thought.

"You little asshole…"

"The motion carries!" Barry yelled slamming his hand on the ground. "Now me! C'mon, bring it on! I'm willing to take any girl! C'mon!"

To everyone's surprise Paul made a suggestion. "The only girl I can think of as annoying as you is Ursula."

Everyone smiled as Barry's face turned blue. "B-but she's crazy! She's mean, obnoxious, selfish, uppity, and-"

"Just like you… literally every word you said just now." Trip said shaking his head. "So, who do you all have planned for me?"

"How about Langley. She seems pretty… monstrous" Ritchie suggested.

"Which means Trip will scare her away for sure! Good thinking Ritchie!" Kenny said snapping.

"Bite me." Trip said flipping them off. "What about you Ritchie?"

"So who's my target?" The young Oak asked before taking a drink from his water bottle.

"How about that Melissa girl?"

Gary spit out his water and then glared at Ash. He knew damn well that he and Melissa weren't on speaking terms… well it was mostly on his part, but still. "What's up Gary? You can't expect me to believe you're still mad she beat you in that kendo tournament. It was in middle school man, let it go." Ritchie said chuckling.

"No!" He said scowling and crossing his arms.

"Well you have to! Cause we voted on it." Trip said bluntly.

Ritchie looked around wondering who they would pick for him, and everyone seemed clueless. They had never seen him flustered by any girl before. They knew he was straight, but as far as having a girl he had eyes for… they didn't know any. "Assunta?" Gary suggested.

"Sure I guess." No one could really see a reason to say no. Ritchie simply shrugged.

"That just leaves out main man Paul. So how about it guys. Should we make it a challenge for him? I think there's a redhead who dying to see this guy ask her out. Zoey would laugh her ass off."

Paul didn't listen and kept on punching. "Not even a flinch? You take the fun out of everything man. We'll it's decided. May the best man win." Barry said smirking.

"I intend to." Drew said combing his hair again.

"C'mon guys, we haven't started the competition yet… and if we had I would have already won." Gary said arrogantly.

"I'm super screwed." Ash said running his hands through his hair.

"You! I'm going to get eaten!" Barry said panicking.

"I'm going to end up having to quite the band before this is over. I just know it." Kenny said slumping to the ground. Paul still said nothing, but the fact that he was hitting the punching back twice as hard as he was before was fairly noticeable.

**A/N: So, I was honestly pretty board. I thought this would be a good idea since it reminded me of hanging out with my friends. Being knuckle heads and making bets. Tell me what you think.**


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